In their various works, researchers, writers, and scholars regularly discuss the public school building level principal. The principal’s role and the tasks performed by the principal are generally recognized as valuable to the educational community. For the most part, the general public has little idea of what the principal’s role entails. Building level principals complete training for the principalship, but their readiness for the principalship is debatable. There is little literature that discusses the first-year principal; the principalship of small, rural schools; and the principalship as experienced by a first-year principal. This study identified what the first-year principal of a rural school encountered during his first year. The study documented events that included school stakeholders such as community members, board members, teachers, students, and central office personnel. The documented events are presented chronologically, beginning with appointment to the principalship and concluding with the final week of the first school year. Events included school finance, student discipline, and curriculum. The research was conducted as an autoethnography, which allowed documentation of the events of the first-year principal from a first-hand perspective. The intricate details provided insight to the first year of administrative duties. Findings determined that the principal’s readiness for assuming the principal’s role had little to do with prior educational training, but more to do with personal qualities and prior job experiences as a coach, teacher, and assistant principal. Discussion and recommendations include the need for preparation programs for rural administrators to recognize they cannot prepare administrators for all decisions they will make, but can prepare them to be decision-makers and leaders. Many duties of this first-year principal were learned on-the-job, including financial matters concerning the handling of school funds, the relationship with the school secretary, and the handling of athletic events.